In U.S. Pat. No. 3,987,037 as well as in U.S. Pat. No. 3,954,475 a two step method is disclosed for preparing chromophore substituted vinyl-halomethyl-s-triazines having the following formula: ##STR1## where Q is bromine or chlorine; Z is --CQ.sub.3, --NH.sub.2, --NHR.sub.1, NR.sub.2, or --OR where R is phenyl or lower alkyl, preferably an alkyl group having no more than 6 carbon atoms; n is an integer from 1 to 3, and W is optionally substituted aromatic or heterocyclic nucleus.
Although 2-(p methoxy styryl)-4,6 bis(trichloromethyl)-s-triazine is one of the especially preferred s-triazines, some of other useful compounds include:
2-styryl-4,6-bis(trichloromethyl)-s-triazine; PA0 2(4-chlorostyryl)-4,6-bis(trichloromethyl)-s-triazine; PA0 2(3,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine; PA0 2(2,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine; PA0 2[(4-dimethylamino)styryl]-4,6-bis(trichloromethyl)-s-triazine; PA0 2(4-pentoxystyryl)-4,6-bis(trichloromethyl)-s-triazine; and PA0 2(4-methoxystyryl)-4-amino-6-trichloromethyl-s-triazine,
In general, an example of the known preparation involved initially making 2,4-bis(trichloromethyl)-6-methyl-s-triazine. Separating this intermediate compound from the resulting reaction procedure, and then condensing it with p-anisaldehyde. More particularly, the initial step involves the preparation of the methyl-halomethyl-s-triazine intermediate by co-trimerization of organic nitriles and haloacetonitriles in accordance with the teachings of Wakabayashi et al., Bulletin of the Chemical Society of Japan, 42, 2924-30 (1969).
The intermediate compound is 2,4-bis-(trichloromethyl)-6-methyl-s-triazine. In practicing the known process in large scale or for commercial operations the isolation of this intermediate compound has proven to be quite difficult, since the crude reaction product must be melted by heating to 110.degree. C. and then subsequently added to water to isolate very sticky material. Consequently, large excess of water and much time is required in order to isolate and purify the intermediate compound.
It would be desirable to have available a process that could be readily adaptable for commercial and continuous operations which avoided the disadvantages of the known two step procedure described in U.S. Pat. No. 3,987,037. It would be particularly advantageous to have a process which did not require the time consuming and cumbersome step of separating the intermediate compound from the crude reaction product obtained in the initial step of the overall procedure. Previous descriptions of the art for the preparation of the 2-(p-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine on scale-up gave very inferior yields. The innovation herein described overcame that limitation.